1. Patent Search
  2. Details

ACTIVE COMPOUND COMBINATIONS AND FUNGICIDE COMPOSITIONS COMPRISING THOSE

20230200391 · 2023-06-29

    Inventors

    Cpc classification

    International classification

    Abstract

    The present invention relates to active compound combinations comprising as compound (A) methyl 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1,2,4-triazol-1-yl)propanoate, 2-[2-chloro-4-(4-chloro-phenoxy)phenyl]-2-hydroxy-3-(1,2,4-triazol-1-yl)propanoic acid or a mixture thereof, as compound (B) at least one fungicide selected from specified inhibitors of the ergosterol synthesis and fungicides capable of having a multisite action, and as compound (C) at least one further fungicide selected from inhibitors of the respiratory chain at complex I or II and specified inhibitors of the respiratory chain at complex III, to compositions comprising such compound combination, and to the use thereof as biologically active agents, especially for control of harmful microorganisms in crop protection and in the protection of industrial materials.

    Claims

    1. An active compound combination comprising (A) as compound (A) methyl 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1,2,4-triazol-1-yl)propanoate, 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1,2,4-triazol-1-yl)propanoic acid or a mixture thereof, (B) as compound (B) at least one further active compound selected from: inhibitors of the ergosterol biosynthesis selected from the group consisting of (1.001) cyproconazole, (1.002) difenoconazole, (1.003) epoxiconazole, (1.004) fenhexamid, (1.005) fenpropidin, (1.006) fenpropimorph, (1.007) fenpyrazamine, (1.008) fluquinconazole, (1.009) flutriafol, (1.010) imazalil, (1.011) imazalil sulfate, (1.012) ipconazole, (1.013) metconazole, (1.014) myclobutanil, (1.015) paclobutrazol, (1.016) prochloraz, (1.017) propiconazole, (1.018) prothioconazole, (1.019) pyrisoxazole, (1.021) tebuconazole, (1.022) tetraconazole, (1.023) triadimenol, (1.024) tridemorph, (1.025) triticonazole, (1.026) (1R,2S,5S)-5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)-cyclopentanol, (1.027) (1S,2R,5R)-5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol, (1.028) (2R)-2-(1-chlorocyclopropyl)-4-[(1R)-2,2-dichlorocyclopropyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol, (1.029) (2R)-2-(1-chloro-cyclopropyl)-4-[(1S)-2,2-dichlorocyclopropyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol, (1.030) (2R)-2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol, (1.031) (2S)-2-(1-chlorocyclopropyl)-4-[(1R)-2,2-dichlorocyclopropyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol, (1.032) (2S)-2-(1-chlorocyclopropyl)-4-[(1S)-2,2-dichlorocyclopropyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol, (1.033) (2S)-2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol, (1.034) (R)-[3-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-1,2-oxazol-4-yl](pyridin-3-yl)methanol, (1.035) (S)-[3-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-1,2-oxazol-4-yl](pyridin-3-yl)methanol, (1.036) [3-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-1,2-oxazol-4-yl](pyridin-3-yl)methanol, (1.037) 1-({(2R,4S)-2-[2-chloro-4-(4-chlorophenoxy)phenyl]-4-methyl-1,3-dioxolan-2-yl}methyl)-1H-1,2,4-triazole, (1.038) 1-({(2S,4S)-2-[2-chloro-4-(4-chlorophenoxy)phenyl]-4-methyl-1,3-dioxolan-2-yl}methyl)-1H-1,2,4-triazole, (1.039) 1-{[3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazol-5-yl thiocyanate, (1.040) 1-{[rel(2R,3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazol-5-yl thiocyanate, (1.041) 1-{[rel(2R,3S)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazol-5-yl thiocyanate, (1.042) 2-[(2R,4R,5R)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.043) 2-[(2R,4R,5S)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.044) 2-[(2R,4S,5R)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.045) 2-[(2R,4S,5S)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.046) 2-[(2S,4R,5R)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.047) 2-[(2S,4R,5S)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.048) 2-[(2S,4S,5R)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.049) 2-[(2S,4S,5S)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.050) 2-[1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.051) 2-[2-chloro-4-(2,4-dichlorophenoxy)phenyl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol, (1.052) 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol, (1.053) 2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol, (1.054) 2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1H-1,2,4-triazol-1-yl)pentan-2-ol, (1.055) mefentrifluconazole, (1.056) 2-{[3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.057) 2-{[rel(2R,3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.058) 2-{[rel(2R,3S)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.059) 5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol, (1.060) 5-(allylsulfanyl)-1-{[3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazole, (1.061) 5-(allylsulfanyl)-1-{[rel(2R,3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazole, (1.062) 5-(allylsulfanyl)-1-{[rel(2R,3S)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazole, (1.063) N′-(2,5-dimethyl-4-{[3-(1,1,2,2-tetrafluoroethoxy)phenyl]sulfanyl}phenyl)-N-ethyl-N-methylimidoformamide, (1.064) N′-(2,5-dimethyl-4-{[3-(2,2,2-trifluoroethoxy)phenyl]sulfanyl}phenyl)-N-ethyl-N-methylimidoformamide, (1.065) N′-(2,5-dimethyl-4-{[3-(2,2,3,3-tetrafluoropropoxy)phenyl]sulfanyl}phenyl)-N-ethyl-N-methylimidoformamide, (1.066) N′-(2,5-dimethyl-4-{[3-(pentafluoroethoxy)phenyl]sulfanyl}phenyl)-N-ethyl-N-methylimidoformamide, (1.067) N′-(2,5-dimethyl-4-{3-[(1,1,2,2-tetrafluoroethyl)sulfanyl]phenoxy}phenyl)-N-ethyl-N-methylimidoformamide, (1.068) N′-(2,5-dimethyl-4-{3-[(2,2,2-trifluoroethyl)sulfanyl]phenoxy}phenyl)-N-ethyl-N-methylimidoformamide, (1.069) N′-(2,5-dimethyl-4-{3-[(2,2,3,3-tetrafluoropropyl)sulfanyl]phenoxy}phenyl)-N-ethyl-N-methylimidoformamide, (1.070) N′-(2,5-dimethyl-4-{3-[(pentafluoroethyl)sulfanyl]phenoxy}phenyl)-N-ethyl-N-methylimidoformamide, (1.071) N′-(2,5-dimethyl-4-phenoxyphenyl)-N-ethyl-N-methylimidoformamide, (1.072) N′-(4-{[3-(difluoromethoxy)phenyl]sulfanyl}-2,5-dimethylphenyl)-N-ethyl-N-methylimidoformamide, (1.073) N′-(4-{3-[(difluoro-methyl)sulfanyl]phenoxy}-2,5-dimethylphenyl)-N-ethyl-N-methylimidoformamide, (1.074) N′-[5-bromo-6-(2,3-dihydro-1H-inden-2-yloxy)-2-methylpyridin-3-yl]-N-ethyl-N-methylimidoformamide, (1.075) N′-{4-[(4,5-dichloro-1,3-thiazol-2-yl)oxy]-2,5-dimethylphenyl}-N-ethyl-N-methylimidoformamide, (1.076) N′-{5-bromo-6-[(1R)-1-(3,5-difluorophenyl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamide, (1.077) N′-{5-bromo-6-[(1S)-1-(3,5-difluorophenyl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamide, (1.078) N′-{5-bromo-6-[(cis-4-isopropylcyclohexyl)oxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamide, (1.079) N′-{5-bromo-6-[(trans-4-isopropylcyclohexyl)oxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamide, (1.080) N′-{5-bromo-6-[1-(3,5-difluorophenyl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamide, and (1.081) ipfentrifluconazole, and one or more fungicides capable of having a multisite action, and (C) as compound (C) at least one further active compound selected from: inhibitors of the respiratory chain at complex I or II, and inhibitors of the respiratory chain at complex III selected from the group consisting of (3.001) ametoctradin, (3.002) amisulbrom, (3.003) azoxystrobin, (3.004) coumethoxystrobin, (3.005) coumoxystrobin, (3.006) cyazofamid, (3.007) dimoxystrobin, (3.008) enoxastrobin, (3.009) famoxadone, (3.010) fenamidone, (3.011) flufenoxystrobin, (3.012) fluoxastrobin, (3.013) kresoxim-methyl, (3.014) metominostrobin, (3.015) orysastrobin, (3.016) picoxystrobin, (3.017) pyraclostrobin, (3.018) pyrametostrobin, (3.019) pyraoxystrobin, (3.020) trifloxystrobin, (3.021) (2E)-2-{2-[({[(1E)-1-(3-{[(E)-1-fluoro-2-phenylvinyl]oxy}phenyl)ethylidene]amino}oxy)methyl]phenyl}-2-(methoxyimino)-N-methylacetamide, (3.022) (2E,3Z)-5-{[1-(4-chlorophenyl)-1H-pyrazol-3-yl]oxy}-2-(methoxyimino)-N,3-dimethylpent-3-enamide, (3.023) (2R)-2-{2-[(2,5-dimethylphenoxy)methyl]phenyl}-2-methoxy-N-methylacetamide, (3.024) (2S)-2-{2-[(2,5-dimethylphenoxy)methyl]phenyl}-2-methoxy-N-methylacetamide, (3.025) fenpicoxamid, (3.026) mandestrobin, (3.027) N-(3-ethyl-3,5,5-trimethylcyclohexyl)-3-formamido-2-hydroxybenzamide, (3.028) (2E,3Z)-5-{[1-(4-chloro-2-fluorophenyl)-1H-pyrazol-3-yl]oxy}-2-(methoxyimino)-N,3-dimethylpent-3-enamide, (3.029) methyl {5-[3-(2,4-dimethylphenyl)-1H-pyrazol-1-yl]-2-methylbenzyl}carbamate, (3.030) metyltetraprole and (3.031) florylpicoxamid.

    2. The active compound combination according to claim 1, wherein compound (A) is methyl 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1,2,4-triazol-1-yl)propanoate.

    3. The active compound combination according to claim 1, wherein compound (B) is selected from inhibitors of the ergosterol biosynthesis selected from the group consisting of (1.001) cyproconazole, (1.002) difenoconazole, (1.003) epoxiconazole, (1.004) fenhexamid, (1.005) fenpropidin, (1.006) fenpropimorph, (1.007) fenpyrazamine, (1.008) fluquinconazole, (1.009) flutriafol, (1.010) imazalil, (1.011) imazalil sulfate, (1.012) ipconazole, (1.013) metconazole, (1.014) myclobutanil, (1.015) paclobutrazol, (1.016) prochloraz, (1.017) propiconazole, (1.018) prothioconazole, (1.019) pyrisoxazole, (1.021) tebuconazole, (1.022) tetraconazole, (1.023) triadimenol, (1.024) tridemorph, (1.025) triticonazole, (1.026) (1R,2S,5S)-5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol, (1.027) (1S,2R,5R)-5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol, (1.028) (2R)-2-(1-chlorocyclopropyl)-4-[(1R)-2,2-dichlorocyclopropyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol, (1.029) (2R)-2-(1-chlorocyclopropyl)-4-[(1S)-2,2-dichlorocyclopropyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol, (1.030) (2R)-2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol, (1.031) (2S)-2-(1-chlorocyclopropyl)-4-[(1R)-2,2-dichlorocyclopropyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol, (1.032) (2S)-2-(1-chlorocyclopropyl)-4-[(1S)-2,2-dichlorocyclopropyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol, (1.033) (2S)-2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol, (1.034) (R)-[3-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-1,2-oxazol-4-yl](pyridin-3-yl)methanol, (1.035) (S)-[3-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-1,2-oxazol-4-yl](pyridin-3-yl)methanol, (1.036) [3-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-1,2-oxazol-4-yl](pyridin-3-yl)methanol, (1.037) 1-({(2R,4S)-2-[2-chloro-4-(4-chlorophenoxy)phenyl]-4-methyl-1,3-dioxolan-2-yl}methyl)-1H-1,2,4-triazole, (1.038) 1-({(2S,4S)-2-[2-chloro-4-(4-chlorophenoxy)phenyl]-4-methyl-1,3-dioxolan-2-yl}methyl)-1H-1,2,4-triazole, (1.039) 1-{[3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazol-5-yl thiocyanate, (1.040) 1-{[rel(2R,3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazol-5-yl thiocyanate, (1.041) 1-{[rel(2R,3S)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazol-5-yl thiocyanate, (1.042) 2-[(2R,4R,5R)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.043) 2-[(2R,4R,5S)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.044) 2-[(2R,4S,5R)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.045) 2-[(2R,4S,5S)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.046) 2-[(2S,4R,5R)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.047) 2-[(2S,4R,5S)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.048) 2-[(2S,4S,5R)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.049) 2-[(2S,4S,5S)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.050) 2-[1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.051) 2-[2-chloro-4-(2,4-dichlorophenoxy)phenyl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol, (1.052) 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol, (1.053) 2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol, (1.054) 2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1H-1,2,4-triazol-1-yl)pentan-2-ol, (1.055) mefentrifluconazole, (1.056) 2-{[3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.057) 2-{[rel(2R,3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.058) 2-{[rel(2R,3S)-3-(2-chlorophenyl)-2-(2,4-difluoro-phenyl)oxiran-2-yl]methyl}-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.059) 5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol, (1.060) 5-(allylsulfanyl)-1-{[3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazole, (1.061) 5-(allylsulfanyl)-1-{[rel(2R,3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazole, (1.062) 5-(allylsulfanyl)-1-{[rel(2R,3S)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazole, (1.063) N′-(2,5-dimethyl-4-{[3-(1,1,2,2-tetrafluoroethoxy)phenyl]sulfanyl}phenyl)-N-ethyl-N-methylimidoformamide, (1.064) N′-(2,5-dimethyl-4-{[3-(2,2,2-trifluoroethoxy)phenyl]sulfanyl}phenyl)-N-ethyl-N-methylimidoformamide, (1.065) N′-(2,5-dimethyl-4-{[3-(2,2,3,3-tetrafluoropropoxy)phenyl]sulfanyl}phenyl)-N-ethyl-N-methylimidoformamide, (1.066) N′-(2,5-dimethyl-4-{[3-(pentafluoroethoxy)phenyl]sulfanyl}phenyl)-N-ethyl-N-methylimidoformamide, (1.067) N′-(2,5-dimethyl-4-{3-[(1,1,2,2-tetrafluoroethyl)sulfanyl]-phenoxy}phenyl)-N-ethyl-N-methylimidoformamide, (1.068) N′-(2,5-dimethyl-4-{3-[(2,2,2-trifluoroethyl)sulfanyl]phenoxy}phenyl)-N-ethyl-N-methylimidoformamide, (1.069) N′-(2,5-dimethyl-4-{3-[(2,2,3,3-tetrafluoropropyl)sulfanyl]phenoxy}phenyl)-N-ethyl-N-methylimidoformamide, (1.070) N′-(2,5-dimethyl-4-{3-[(pentafluoroethyl)sulfanyl]phenoxy}phenyl)-N-ethyl-N-methylimidoformamide, (1.071) N′-(2,5-dimethyl-4-phenoxyphenyl)-N-ethyl-N-methylimidoformamide, (1.072) N′-(4-{[3-(difluoromethoxy)phenyl]sulfanyl}-2,5-dimethylphenyl)-N-ethyl-N-methylimidoformamide, (1.073) N′-(4-{3-[(difluoromethyl)sulfanyl]phenoxy}-2,5-dimethylphenyl)-N-ethyl-N-methylimidoformamide, (1.074) N′-[5-bromo-6-(2,3-dihydro-1H-inden-2-yloxy)-2-methylpyridin-3-yl]-N-ethyl-N-methylimidoformamide, (1.075) N′-{4-[(4,5-dichloro-1,3-thiazol-2-yl)oxy]-2,5-dimethylphenyl}-N-ethyl-N-methylimidoformamide, (1.076) N′-{5-bromo-6-[(1R)-1-(3,5-difluorophenyl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamide, (1.077) N′-{5-bromo-6-[(1S)-1-(3,5-difluorophenyl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamide, (1.078) N′-{5-bromo-6-[(cis-4-isopropylcyclohexyl)oxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamide, (1.079) N′-{5-bromo-6-[(trans-4-isopropylcyclohexyl)oxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamide, (1.080) N′-{5-bromo-6-[1-(3,5-difluorophenyl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamide, and (1.081) ipfentrifluconazole, and compounds capable of having a multisite action selected from the group consisting of (5.001) bordeaux mixture, (5.002) captafol, (5.003) captan, (5.004) chlorothalonil, (5.005) copper hydroxide, (5.006) copper naphthenate, (5.007) copper oxide, (5.008) copper oxychloride, (5.009) copper (2+) sulfate, (5.010) dithianon, (5.011) dodine, (5.012) folpet, (5.013) mancozeb, (5.014) maneb, (5.015) metiram, (5.016) metiram zinc, (5.017) oxine-copper, (5.018) propineb, (5.019) sulfur and sulfur preparations including calcium polysulfide, (5.020) thiram, (5.021) zineb, (5.022) ziram, and (5.023) 6-ethyl-5,7-dioxo-6,7-dihydro-5H-pyrrolo[3′,4′:5,6][1,4]dithiino[2,3-c][1,2]thiazole-3-carbonitrile.

    4. The active compound combination according to claim 1, wherein compound (B) is selected from (1.012) ipconazole, (1.018) prothioconazole, (1.021) tebuconazole, (5.003) captan, (5.004) chlorothalonil, (5.010) dithianon, (5.012) folpet, (5.013) mancozeb, (5.015) metiram, (5.016) metiram zinc, (5.018) propineb and (5.020) thiram, optionally from (1.018) prothioconazole and (5.013) mancozeb.

    5. The active compound combination according to claim 1, wherein compound (C) is selected from inhibitors of the respiratory chain at complex I or II selected from the group consisting of (2.001) benzovindiflupyr, (2.002) bixafen, (2.003) boscalid, (2.004) carboxin, (2.005) fluopyram, (2.006) flutolanil, (2.007) fluxapyroxad, (2.008) furametpyr, (2.009) isofetamid, (2.010) isopyrazam (anti-epimeric enantiomer 1R,4S,9S), (2.011) isopyrazam (anti-epimeric enantiomer 1S,4R,9R), (2.012) isopyrazam (anti-epimeric racemate 1RS,4SR,9SR), (2.013) isopyrazam (mixture of syn-epimeric racemate 1RS,4SR,9RS and anti-epimeric racemate 1RS,4SR,9SR), (2.014) isopyrazam (syn-epimeric enantiomer 1R,4S,9R), (2.015) isopyrazam (syn-epimeric enantiomer 1S,4R,9S), (2.016) isopyrazam (syn-epimeric racemate 1RS,4SR,9RS), (2.017) penflufen, (2.018) penthiopyrad, (2.019) pydiflumetofen, (2.020) Pyraziflumid, (2.021) sedaxane, (2.022) 1,3-dimethyl-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)-1H-pyrazole-4-carboxamide, (2.023) 1,3-dimethyl-N-[(3R)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazole-4-carboxamide, (2.024) 1,3-dimethyl-N-[(3S)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazole-4-carboxamide, (2.025) 1-methyl-3-(trifluoromethyl)-N-[2′-(trifluoromethyl)biphenyl-2-yl]-1H-pyrazole-4-carboxamide, (2.026) 2-fluoro-6-(trifluoromethyl)-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)benzamide, (2.027) inpyrfluxam, (2.028) 3-(difluoromethyl)-1-methyl-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)-1H-pyrazole-4-carboxamide, (2.029) 3-(difluoromethyl)-1-methyl-N-[(3S)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazole-4-carboxamide, (2.030) fluindapyr, (2.031) 3-(difluoromethyl)-N-[(3R)-7-fluoro-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1-methyl-1H-pyrazole-4-carboxamide, (2.032) 3-(difluoromethyl)-N-[(3S)-7-fluoro-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1-methyl-1H-pyrazole-4-carboxamide, (2.033) 5,8-difluoro-N-[2-(2-fluoro-4-{[4-(trifluoromethyl)pyridin-2-yl]oxy}phenyl)ethyl]quinazolin-4-amine, (2.034) N-(2-cyclopentyl-5-fluorobenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.035) N-(2-tert-butyl-5-methylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.036) N-(2-tert-butylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.037) N-(5-chloro-2-ethylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.038) isoflucypram, (2.039) N-[(1R,4S)-9-(dichloromethylene)-1,2,3,4-tetrahydro-1,4-methanonaphthalen-5-yl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide, (2.040) N-[(1S,4R)-9-(dichloromethylene)-1,2,3,4-tetrahydro-1,4-methanonaphthalen-5-yl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide, (2.041) N-[1-(2,4-dichlorophenyl)-1-methoxypropan-2-yl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide, (2.042) N-[2-chloro-6-(trifluoromethyl)benzyl]-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.043) N-[3-chloro-2-fluoro-6-(trifluoromethyl)benzyl]-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.044) N-[5-chloro-2-(trifluoromethyl)benzyl]-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.045) N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-N-[5-methyl-2-(trifluoromethyl)benzyl]-1H-pyrazole-4-carboxamide, (2.046) N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-fluoro-6-isopropylbenzyl)-1-methyl-1H-pyrazole-4-carboxamide, (2.047) N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-isopropyl-5-methylbenzyl)-1-methyl-1H-pyrazole-4-carboxamide, (2.048) N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-isopropylbenzyl)-1-methyl-1H-pyrazole-4-carbothioamide, (2.049) N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-isopropylbenzyl)-1-methyl-1H-pyrazole-4-carboxamide, (2.050) N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(5-fluoro-2-isopropylbenzyl)-1-methyl-1H-pyrazole-4-carboxamide, (2.051) N-cyclopropyl-3-(difluoromethyl)-N-(2-ethyl-4,5-dimethylbenzyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.052) N-cyclopropyl-3-(difluoromethyl)-N-(2-ethyl-5-fluorobenzyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.053) N-cyclopropyl-3-(difluoromethyl)-N-(2-ethyl-5-methylbenzyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.054) N-cyclopropyl-N-(2-cyclopropyl-5-fluorobenzyl)-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.055) N-cyclopropyl-N-(2-cyclopropyl-5-methylbenzyl)-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.056) N-cyclopropyl-N-(2-cyclopropylbenzyl)-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.057) pyrapropoyne, (2.058) N-[rac-(1S,2S)-2-(2,4-dichlorophenyl)cyclobutyl]-2-(trifluoromethyl)nicotinamide, (2.059) N-[(1S,2S)-2-(2,4-dichlorophenyl)cyclobutyl]-2-(trifluoromethyl)nicotinamide and (2.060) cyclobutrifluram, and inhibitors of the respiratory chain at complex III selected from the group consisting of (3.001) ametoctradin, (3.002) amisulbrom, (3.003) azoxystrobin, (3.004) coumethoxystrobin, (3.005) coumoxystrobin, (3.006) cyazofamid, (3.007) dimoxystrobin, (3.008) enoxastrobin, (3.009) famoxadone, (3.010) fenamidone, (3.011) flufenoxystrobin, (3.012) fluoxastrobin, (3.013) kresoxim-methyl, (3.014) metominostrobin, (3.015) orysastrobin, (3.016) picoxystrobin, (3.017) pyraclostrobin, (3.018) pyrametostrobin, (3.019) pyraoxystrobin, (3.020) trifloxystrobin, (3.021) (2E)-2-{2-[({[(1E)-1-(3-{[(E)-1-fluoro-2-phenylvinyl]oxy}phenyl)ethylidene]amino}oxy)methyl]phenyl}-2-(methoxy-imino)-N-methylacetamide, (3.022) (2E,3Z)-5-{[1-(4-chlorophenyl)-1H-pyrazol-3-yl]oxy}-2-(methoxyimino)-N,3-dimethylpent-3-enamide, (3.023) (2R)-2-{2-[(2,5-dimethylphenoxy)methyl]phenyl}-2-methoxy-N-methylacetamide, (3.024) (2S)-2-{2-[(2,5-dimethylphenoxy)methyl]phenyl}-2-methoxy-N-methylacetamide, (3.025) fenpicoxamid, (3.026) mandestrobin, (3.027) N-(3-ethyl-3,5,5-trimethylcyclohexyl)-3-formamido-2-hydroxybenzamide, (3.028) (2E,3Z)-5-{[1-(4-chloro-2-fluorophenyl)-1H-pyrazol-3-yl]oxy}-2-(methoxyimino)-N,3-dimethylpent-3-enamide, (3.029) methyl {5-[3-(2,4-dimethylphenyl)-1H-pyrazol-1-yl]-2-methylbenzyl}carbamate, (3.030) metyltetraprole and (3.031) florylpicoxamid.

    6. The active compound combination according to claim 1, wherein compound (C) is selected from (2.005) fluopyram, (2.017) penflufen, (2.027) inpyrfluxam, (2.038) isoflucypram, (2.060) cyclobutrifluram, (3.012) fluoxastrobin, (3.020) trifloxystrobin and (3.030) metyltetraprole.

    7. The active compound combination according to claim 1, wherein the compound combination is selected from the following combinations: (I-1)+(1.018)+(2.005), (I-1)+(1.018)+(2.017), (I-1)+(1.018)+(2.027), (I-1)+(1.018)+(2.038), (I-1)+(1.018)+(2.060), (I-1)+(1.018)+(3.012), (I-1)+(1.018)+(3.020), (I-1)+(1.018)+(3.030), (I-1)+(5.013)+(2.005), (I-1)+(5.013)+(2.017), (I-1)+(5.013)+(2.027), (I-1)+(5.013)+(2.038), (I-1)+(5.013)+(2.060), (I-1)+(5.013)+(3.012), (I-1)+(5.013)+(3.020), (I-1)+(5.013)+(3.030).

    8. The active compound combination according to claim 1, wherein the weight ratio of compound(s) (A) to compound(s) (B) is from 1000:1 to 1:1000 and the weight ratio of compound(s) (A) to compound(s) (C) is from 1000:1 to 1:1000.

    9. The active compound combination according to claim 1, wherein exactly 1 compound (B) is present.

    10. The active compound combination according claim 1, wherein exactly 1 compound (C) is present.

    11. A composition for controlling one or more harmful microorganisms in crop protection and/or in protection of one or more materials, said composition comprising a content of an active compound combination according to claim 1, in addition to at least one carrier and/or surfactant.

    12. A method for controlling one or more harmful microorganisms in crop protection and/or in protection of one or more materials, comprising applying an active compound combination according to claim 1 or a composition thereof to one or more harmful microorganisms and/or a habitat thereof.

    13. A product comprising an active compound combination according to claim 1 or a composition thereof for treatment of one or more transgenic plants.

    14. A product comprising an active compound combination according to claim 1 or a composition thereof for treatment of seed.

    15. Seed coated with an active compound combination according to claim 1 or a composition thereof.

    Description

    EXAMPLES

    [0415] The advanced fungicidal activity of the active compound combinations according to the invention is evident from the examples below. While the individual active compounds exhibit weaknesses with regard to the fungicidal activity, the combinations have an activity which exceeds a simple addition of activities.

    [0416] A synergistic effect of fungicides is always present when the fungicidal activity of the active compound combinations exceeds the total of the activities of the active compounds when applied individually. The expected activity for a given combination of two active compounds can be calculated as follows (cf. Colby, S. R., “Calculating Synergistic and Antagonistic Responses of Herbicide Combinations”, Weeds 1967, 15, 20-22):

    [0417] If

    [0418] X is the efficacy when active compound A is applied at an application rate of m ppm (or g/ha),

    [0419] Y is the efficacy when active compound B is applied at an application rate of n ppm (or g/ha), and

    [0420] E is the efficacy when the active compounds A and B are applied at application rates of m and n ppm (or g/ha), respectively,

    [0421] then

    [00001] E = X + Y - X .Math. Y 1 ⁢ 0 ⁢ 0

    [0422] For ternary mixtures the following Colby equation results:

    [0423] If

    [0424] X is the efficacy when active compound A is applied at an application rate of m ppm (or g/ha),

    [0425] Y is the efficacy when active compound B is applied at an application rate of n ppm (or g/ha),

    [0426] Z is the efficacy when active compound C is applied at an application rate of o ppm (or g/ha), and

    [0427] E is the efficacy when the active compounds A, B and C are applied at application rates of m, n and o ppm (or g/ha), respectively,

    [0428] then

    [00002] E = X + Y + Z - X .Math. Y 1 ⁢ 0 ⁢ 0 - X .Math. Z 1 ⁢ 0 ⁢ 0 - Y .Math. Z 1 ⁢ 0 ⁢ 0 + X .Math. Y .Math. Z 100 .Math. 100

    [0429] The degree of efficacy, expressed in % is denoted. 0% means an efficacy which corresponds to that of the control while an efficacy of 100% means that no disease is observed.

    [0430] If the actual fungicidal activity exceeds the calculated value, then the activity of the combination is superadditive, i.e. a synergistic effect exists. In this case, the efficacy which was actually observed must be greater than the value for the expected efficacy (E) calculated from the abovementioned formula.

    [0431] A further way of demonstrating a synergistic effect is the method of Tammes (cf. “Isoboles, a graphic representation of synergism in pesticides” in Neth. J. Plant Path., 1964, 70, 73-80).

    Example A: In Vitro-Test with Fungal Microorganisms

    [0432] Wells of 96-well microtiter plates are filled with 30 μl of a preparation of test compound or compound combination in methanol+emulsifier alkylaryl-polyglycol-ether. Thereafter, the solvent is evaporated in a hood. At the next step, into each well 200 μl of liquid growth medium is given, that has been amended with an appropriate concentration of spores or mycelium suspension of the test fungus.

    [0433] With the aid of a photometer the extinction in all wells is measured at the wavelength of 600 nm.

    [0434] The microtiter plates are incubated for 3 to 7 days at 20° C. and 85% relative humidity. After the incubation inhibition of growth is determined photometrically. Efficacy is calculated in relation to the untreated control, 0% efficacy means fungal growth as high as in untreated control while 100% efficacy means no fungal growth is measured.

    [0435] The tables below clearly show that the observed efficacy of the active compound combination according to the invention is greater than the calculated activity, i.e. a synergistic effect is present.

    TABLE-US-00001 TABLE A1 in vitro -Test with Alternaria alternata (1.018) (2.038) (3.012) (5.013) (2.005) (2.060) Colby (I-1) prothioconazole isoflucypram fluoxastrobin mancozeb fluopyram cyclobutrifluram efficacy expected (ppm) (ppm) (ppm) (ppm) (ppm) (ppm) (ppm) ratio % value % 0.5 56 0.10 7 0.02 1 0.1 37 0.02 13 0.004 26 1 76 0.5 0.1 1 1:0.2:2 93 93 0.10 0.02 1 1:0.2:10 97 80 0.02 0.004 1 1:0.2:50 88 82 0.5 56 0.10 7 0.1 37 0.02 13 10 100 0.4 87 0.5 0.1 10 1:0.2:20 100 100 0.5 0.1 0.4 1:0.2:0.8 97 96 0.1 0.2 10 1:0.2:100 100 100 0.1 0.2 0.4 1:0.2:4 91 89 2.5 92 0.02 0 20 74 0.16 0 20 89 0.16 67 2.5 20 20 1:8:8 100 100 2.5 0.16 0.16 1:8:0.064 99 92 0.02 20 20 1:8:1000 99 89 0.02 0.16 0.16 1:8:8 72 67 0.02 0 0.16 0 5 88 0.04 80 0.02 0.16 5 1:8:250 89 88 0.02 0.16 0.04 1:8:2 87 80

    TABLE-US-00002 TABLE A2 in vitro -Test with Alternaria alternata (5.013) (3.020) (2.017) Colby (I-1) mancozeb trifloxystrobin penflufen expected (ppm) (ppm) (ppm) (ppm) ratio efficacy % value % 0.1 22 0.8 1 1 100 0.04 62 0.008 22 0.1 0.8 1 1:8:10 99 100 0.1 0.8 0.04 1:8:0.4 76 71 0.1 0.8 0.008 1:8:0.08 48 40 0.1 27 0.02 0 0.8 0 0.16 0 1 65 0.04 10 0.1 0.8 1 1:8:10 92 75 0.1 0.8 0.04 1:8:0.4 57 35 0.02 0.16 1 1:8:50 74 65 0.02 0.16 0.04 1:8:2 20 10

    TABLE-US-00003 TABLE B1 in vitro -Test with Botrytis cinerea Colby (5.013) (2.005) expected (I-1) mancozeb fluopyram value (ppm) (ppm) (ppm) ratio efficacy % % 0.1 12 0.02 3 0.8 6 0.16 4 20 97 0.8 77 0.16 48 0.1 0.8 20 1:8:200 98 97 0.1 0.8 0.8 1:8:8 82 81 0.1 0.8 0.16 1:8:16 64 57 0.02 0.16 20 1:8:1000 99 97 0.02 0.16 0.8 1:8:40 83 79 0.02 0.16 0.16 1:8:8 58 52

    TABLE-US-00004 TABLE B2 in vitro -Test with Botrytis cinerea (5.013) (2.060) (2.038) (3.020) (3.030) Colby (I-1) mancozeb cyclobutrifluram isoflucypram trifloxystrobin metyltetraprole expected (ppm) (ppm) (ppm) (ppm) (ppm) (ppm) ratio efficacy % value % 0.1 12 0.02 3 0.8 6 0.16 4 1 92 0.2 77 0.04 49 0.1 0.8 1 1:8:10 93 94 0.1 0.8 0.2 1:8:2 83 81 0.1 0.8 0.04 1:8:0.4 66 57 0.02 0.16 1 1:8:50 93 93 0.02 0.16 0.2 1:8:10 81 78 0.02 0.16 0.04 1:8:2 63 53 0.1 14 0.2 0 0.8 4 0.16 2 1 86 0.2 74 0.1 0.8 1 1:8:10 88 88 0.1 0.8 0.2 1:8:2 81 79 0.2 0.16 1 1:8:50 87 86 0.2 0.16 0.2 1:8:10 80 75 0.5 27 0.1 0 0.02 0 4 6 0.8 0 0.16 0 0.2 13 0.04 17 0.008 5 0.5 4 0.2 1:8:0.4 61 41 0.1 0.8 0.2 1:8:2 53 13 0.1 0.8 0.04 1:8:0.4 25 17 0.1 0.8 0.008 1:8:0.08 4 5 0.02 0.16 0.2 1:8:10 50 13 0.02 0.16 0.04 1:8:2 40 17 0.02 0.16 0.008 1:8:0.4 23 5 0.5 27 0.1 0 0.02 0 4 6 0.8 0 0.16 0 10 81 2 41 0.4 34 0.008 11 0.5 4 2 1:8:4 65 60 0.5 4 0.4 1:8:0.8 73 54 0.1 0.8 2 1:8:20 63 41 0.1 0.8 0.4 1:8:4 36 34 0.02 0.16 10 1:8:500 83 81 0.02 0.16 2 1:8:100 59 41 0.02 0.16 0.4 1:8:20 44 34 0.02 0.16 0.008 1:8:4 29 11

    TABLE-US-00005 TABLE C1 in vitro -Test with Cercospora beticola (1.018) prothio- (2.005) (2.038) Colby (I-1) conazole fluopyram isoflucypram expected (ppm) (ppm) (ppm) (ppm) ratio efficacy % value % 2.5 99 0.02 8 0.5 96 0.004 6 20 31 4 11 0.8 0 0.16 25 2.5 0.5 20 1:0.2:8 99 100 2.5 0.5 4 1:0.2:1.6 100 100 2.5 0.5 0.8 1:0.2:0.32 100 100 2.5 0.5 0.16 1:0.2:0.064 100 100 0.02 0.004 20 1:0.2:1000 63 40 0.02 0.004 4 1:0.2:200 55 23 0.02 0.004 0.8 1:0.2:40 36 14 0.02 0.004 0.16 1:0.2:8 66 36 2.5 100 0.5 100 0.02 6 0.5 100 0.1 100 0.004 22 1 68 2.5 0.5 1 1:0.2:0.4 100 100 0.5 0.1 1 1:0.2:2 98 100 0.02 0.004 1 1:0.2:50 84 76

    TABLE-US-00006 TABLE C2 in vitro -Test with Cercospora beticola (5.013) (2.005) (2.038) Colby (I-1) mancozeb fluopyram isoflucypram expected (ppm) (ppm) (ppm) (ppm) ratio efficacy % value % 2.5 100 0.02 18 20 100 0.16 32 20 0 2.5 20 20 1:8:8 100 100 0.02 0.16 20 1:8:1000 78 44 2.5 99 0.02 7 20 98 0.16 14 1 60 0.04 0 2.5 20 1 1:8:0.4 100 100 2.5 20 0.04 1:8:0.016 100 100 0.02 0.16 1 1:8:50 78 68 0.02 0.16 0.04 1:8:2 40 20

    TABLE-US-00007 TABLE D1 in vitro -Test with Colletotrichum coccodes (1.018) (3.012) (3.020) (3.030) Colby (I-1) prothioconazole fluoxastrobin trifloxystrobin metyltetraprole expected (ppm) (ppm) (ppm) (ppm) (ppm) ratio efficacy % value % 0.1 0 0.02 3 0.02 12 0.004 0 10 95 2 83 0.1 0.02 10 1:0.2:100 96 95 0.1 0.02 2 1:0.2:20 85 85 0.02 0.004 10 1:0.2:500 96 95 0.02 0.004 2 1:0.2:100 89 84 0.02 0 0.004 0 1 96 0.04 62 0.008 7 0.02 0.004 1 1:0.2:50 96 96 0.02 0.004 0.04 1:0.2:2 67 62 0.02 0.004 0.008 1:0.2:0.4 41 7 0.1 0 0.02 0 0.02 6 0.004 0 10 100 0.4 73 0.1 0.02 10 1:0.2:100 100 100 0.1 0.02 0.4 1:0.2:4 89 75 0.02 0.004 10 1:0.2:500 99 100 0.02 0.004 0.4 1:0.2:20 85 73

    TABLE-US-00008 TABLE D2 in vitro -Test with Colletotrichum coccodes (5.013) (2.060) (3.012) (3.030) Colby (I-1) mancozeb cyclobutrifluram fluoxastrobin metyltetraprole expected (ppm) (ppm) (ppm) (ppm) (ppm) ratio efficacy % value % 0.1 0 0.8 0 5 12 1 0 0.2 0 0.04 0 0.1 0.8 5 1:8:50 38 12 0.1 0.8 1 1:8:10 0 0 0.1 0.8 0.2 1:8:2 13 0 0.1 0.8 0.04 1:8:0.4 0 0 0.5 32 0.1 0 4 24 0.8 16 10 96 2 85 0.5 4 10 1:8:20 100 98 0.5 4 2 1:8:4 95 92 0.1 0.8 10 1:8:100 97 96 0.1 0.8 2 1:8:20 89 87 0.1 0 0.8 14 10 100 0.08 25 0.1 0.8 10 1:8:100 100 100 0.1 0.8 0.08 1:8:0.8 52 35

    TABLE-US-00009 TABLE E1 in vitro -Test with Cordana musae (1.018) (2.060) (2.027) (3.012) Colby (I-1) prothioconazole cyclobutrifluram inpyrfluxam fluoxastrobin expected (ppm) (ppm) (ppm) (ppm) (ppm) ratio efficacy % value % 0.02 0 0.004 2 5 42 0.2 0 0.04 0 0.02 0.004 5 1:0.2:250 57 43 0.02 0.004 0.2 1:0.2:10 3 3 0.02 0.004 0.04 1:0.2:2 3 3 2.5 99 0.1 3 0.02 0 0.5 99 0.02 6 0.004 3 1 3 2.5 0.5 1 1:0.2:0.4 100 100 0.1 0.02 1 1:0.2:10 14 11 0.02 0.004 1 1:0.2:50 31 7 2.5 99 0.1 0 0.02 0 0.5 99 0.02 13 0.004 0 10 81 2 74 2.5 0.5 10 1:0.2:4 100 100 2.5 0.5 2 1:0.2:0.8 100 100 0.1 0.02 10 1:0.2:100 79 83 0.1 0.02 2 1:0.2:20 80 77 0.02 0.004 10 1:0.2:500 89 81 0.02 0.004 2 1:0.2:100 76 74

    TABLE-US-00010 TABLE E2 in vitro -Test with Cordana musae (1.018) (3.030) (5.013) (2.060) Colby (I-1) prothioconazole metyltetraprole mancozeb cyclobutrifluram expected (ppm) (ppm) (ppm) (ppm) (ppm) ratio efficacy % value % 0.1 5 0.02 0 0.02 19 0.004 0 10 93 0.08 44 0.1 0.02 10 1:0.2:100 95 94 0.1 0.02 0.08 1:0.2:0.8 62 57 0.02 0.004 10 1:0.2:500 95 93 0.02 0.004 0.08 1:0.2:4 45 44 0.5 15 0.1 0 0.02 0 4 12 0.8 0 0.16 0 5 6 0.5 4 5 1:8:10 30 30 0.1 0.8 5 1:8:50 21 6 0.02 0.16 5 1:8:250 7 6 0.1 0 10 86 2 78 0.4 70 0.8 0 0.1 10 0.8 1:100:8 92 86 0.1 2 0.8 1:20:8 81 78 0.1 0.4 0.8 1:4:8 72 70

    TABLE-US-00011 TABLE F1 in vitro -Test with Diaporthe citri (1.018) (2.027) effi- Colby (I-1) prothioconazole inpyrfluxam cacy expected (ppm) (ppm) (ppm) ratio % value % 2.5 98 0.5 96 0.02 12 0.5 99 0.1 98 0.004 14 1 86 2.5 0.5 1 1:0.5:2.5 99 100 0.5 0.1 1 1:0.5:2 99 100 0.02 0.004 1 1:0.5:50 93 89

    TABLE-US-00012 TABLE F2 in vitro -Test with Diaporthe citri (5.013) (2.027) (3.030) Colby (I-1) mancozeb inpyrfluxam metyltetraprole expected (PPm) (ppm) (ppm) (ppm) ratio efficacy % value % 2.5 98 0.1 0 0.02 0 20 96 0.8 0 0.16 0 1 84 2.5 20 1 1:8:0.4 99 100 0.1 0.8 1 1:8:10 87 84 0.02 0.16 1 1:8:50 93 84 0.1 7 0.02 0 0.8 6 0.16 11 10 99 2 95 0.1 0.8 10 1:8:100 100 99 0.1 0.8 2 1:8:20 96 96 0.02 0.16 10 1:8:500 100 99 0.02 0.16 2 1:8:100 99 96

    TABLE-US-00013 TABLE G1 in vitro -Test with Fusarium culmorum (2.038) (1.018) (2.060) (3.012) (5.013) Colby (I-1) isoflucypram prothioconazole cyclobutrifluram fluoxastrobin mancozeb efficacy expected (ppm) (ppm) (ppm) (ppm) (ppm) (ppm) ratio % value % 2.5 67 0.1 0 0.5 98 0.02 0 5 56 0.2 57 2.5 0.5 5 1:0.2:2 100 100 2.5 0.5 0.2 1:0.2:0.08 97 100 0.1 0.02 5 1:0.2:50 62 55 0.1 0.02 0.2 1:0.2:2 60 57 2.5 98 0.1 11 0.02 14 0.04 0 0.5 99 0.02 0 0.004 3 2.5 0.04 0.5 1:0.016:0.2 99 100 0.1 0.04 0.02 1:0.4:0.2 24 11 0.02 0.04 0.004 1:2:0.2 22 17 2.5 98 0.1 11 0.02 14 0.5 99 0.02 0 0.004 3 10 47 2.5 0.5 10 1:0.2:4 100 100 0.1 0.02 10 1:0.2:100 60 53 0.02 0.004 10 1:0.2:500 61 55 0.5 0 5 56 0.2 48 0.04 47 4 0 0.5 5 4 1:10:8 58 56 0.5 0.2 4 1:0.4:8 51 48 0.5 0.04 4 1:0.08:8 50 47

    TABLE-US-00014 TABLE G2 in vitro -Test with Fusarium culmorum (5.013) (3.012) (3.020) Colby (I-1) mancozeb fluoxastrobin trifloxystrobin expected (ppm) (ppm) (ppm) (ppm) ratio efficacy % value % 0.02 4 0.16 0 10 54 2 34 0.4 26 0.02 0.16 10 1:8:500 62 56 0.02 0.16 2 1:8:100 53 36 0.02 0.16 0.4 1:8:20 38 29 0.1 14 0.02 10 0.8 0 0.16 0 0.04 19 0.008 0 0.1 0.8 0.04 1:8:0.4 33 30 0.1 0.8 0.008 1:8:0.08 23 14 0.02 0.16 0.04 1:8:2 44 27 0.02 0.16 0.008 1:8:0.4 29 10

    TABLE-US-00015 TABLE H1 in vitro -Test with Parastagonospora nodorum (1.018) (2.005) (2.060) (2.017) Colby (I-1) prothioconazole fluopyram cyclobutrifluram penflufen expected (ppm) (ppm) (ppm) (ppm) (ppm) ratio efficacy % value % 0.5 98 0.02 2 0.1 97 0.004 23 20 86 4 49 0.5 0.1 20 1:0.2:40 99 100 0.5 0.1 4 1:0.2:8 100 100 0.02 0.004 20 1:0.2:1000 99 89 0.02 0.004 4 1:0.2:200 73 62 2.5 96 0.5 98 0.1 87 0.02 2 0.5 97 0.1 97 0.02 83 0.004 23 5 0 2.5 0.5 5 1:0.2:2 100 100 0.5 0.1 5 1:0.2:10 100 100 0.1 0.02 5 1:0.2:50 98 98 0.02 0.004 5 1:0.2:250 85 25 0.5 98 0.02 0 0.1 97 0.004 0 5 42 0.2 0 0.5 0.1 5 1:0.2:10 100 100 0.5 0.1 0.2 1:0.2:0.4 100 100 0.02 0.004 5 1:0.2:250 56 42 0.02 0.004 0.2 1:0.2:10 0 0

    TABLE-US-00016 TABLE H2 in vitro -Test with Parastagonospora nodorum (1.018) (3.020) (5.013) (2.060) (2.017) (2.027) Colby (I-1) prothioconazole trifloxystrobin mancozeb cyclobutrifluram penflufen inpyrfluxam efficacy expected (ppm) (ppm) (ppm) (ppm) (ppm) (ppm) (ppm) ratio % value % 0.02 0 0.004 2 1 97 0.04 73 0.008 32 0.02 0.004 1 1:0.2:50 98 97 0.02 0.004 0.04 1:0.2:2 61 74 0.02 0.004 0.008 1:0.2:0.4 38 33 0.02 0 0.16 0 5 98 0.2 13 0.04 5 0.02 0.16 5 1:8:250 99 98 0.02 0.16 0.2 1:8:10 21 13 0.02 0.16 0.04 1:8:2 5 5 0.02 0 0.16 0 5 48 1 17 0.2 4 0.04 0 0.02 0.16 5 1:8:250 48 48 0.02 0.16 1 01:08:50 17 17 0.02 0.16 0.2 1:8:10 6 4 0.02 0.16 0.04 1:8:2 0 0 0.02 0 0.16 0 1 0.04 0.008 0.02 0.16 1 1:8:50 48 34 0.02 0.16 0.04 1:8:2 4 1 0.02 0.16 0.008 1:8:0.4 3 0

    TABLE-US-00017 TABLE I1 in vitro -Test with Ustilago segetum var. avenae Colby (1.018) (3.030) effi- expec- (I-1) prothioconazole metyltetraprole cacy ted (ppm) (ppm) (ppm) ratio % value % 2.5 98 0.5 96 0.02 9 0.5 99 0.1 99 0.004 45 10 34 2.5 0.5 10 1:0.2:4 99 100 0.5 0.1 10 1:0.2:20 99 100 0.02 0.004 10 1:0.2:500 72 67